Enantioselective Hydrolysis of d,l‐Menthyl Benzoate to L‐(–)‐Menthol by Recombinant Candida rugosa Lipase LIP1
Identifieur interne : 000412 ( Main/Exploration ); précédent : 000411; suivant : 000413Enantioselective Hydrolysis of d,l‐Menthyl Benzoate to L‐(–)‐Menthol by Recombinant Candida rugosa Lipase LIP1
Auteurs : Sandra Vorlová ; Uwe Bornscheuer [Allemagne] ; Ian Gatfield [Allemagne] ; Jens-Michael Hilmer [Allemagne] ; Heinz-Juergen Bertram [Allemagne] ; Rolf Schmid [Allemagne]Source :
- Advanced Synthesis & Catalysis [ 1615-4150 ] ; 2002-12.
English descriptors
- Teeft :
- Amano, Benzoate, Biotechnol, Candida, Candida rugosa, Catal, Chem, Different temperatures, Enantiomeric, Enantiomeric purity, Enantioselective, Enantioselective hydrolysis, Enantioselective method, Enantioselectivity, Ester, Ethyl acetate, High enantioselectivity, Isoenzyme, Isoenzyme lip1, Kinetic resolution, Lip1, Lipase, Menthol, Menthyl, Menthyl benzoate, Optical purity, Reaction mixture, Reaction product, Recombinant, Rugosa, Sodium phosphate buffer, Stereoselective synthesis, Synth.
Abstract
The stereoselective synthesis of L‐menthol is an attractive process in the flavor and fragrance industry. One promising way to obtain optically pure menthol is the enantioselective hydrolysis of menthol esters under enzymatic catalysis. We developed an effective and highly enantioselective method for the synthesis of L‐(−)‐menthol (>99% EE) by hydrolyzing the key industrial starting compound, d, l‐menthyl benzoate. The enzyme of choice was the lipase from Candida rugosa (CRL). While commercially available preparations of this lipase showed only minor selectivity (E=15), excellent enantiomeric purity (E>100) was achieved using the heterologously expressed isoenzyme LIP1.
Url:
DOI: 10.1002/1615-4169(200212)344:10<1152::AID-ADSC1152>3.0.CO;2-N
Affiliations:
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lip1</term><term>Kinetic resolution</term><term>Lip1</term><term>Lipase</term><term>Menthol</term><term>Menthyl</term><term>Menthyl benzoate</term><term>Optical purity</term><term>Reaction mixture</term><term>Reaction product</term><term>Recombinant</term><term>Rugosa</term><term>Sodium phosphate buffer</term><term>Stereoselective synthesis</term><term>Synth</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The stereoselective synthesis of L‐menthol is an attractive process in the flavor and fragrance industry. One promising way to obtain optically pure menthol is the enantioselective hydrolysis of menthol esters under enzymatic catalysis. We developed an effective and highly enantioselective method for the synthesis of L‐(−)‐menthol (>99% EE) by hydrolyzing the key industrial starting compound, d, l‐menthyl benzoate. The enzyme of choice was the lipase from Candida rugosa (CRL). While commercially available preparations of this lipase showed only minor selectivity (E=15), excellent enantiomeric purity (E>100) was achieved using the heterologously expressed isoenzyme LIP1.</div></front></TEI><affiliations><list><country><li>Allemagne</li></country></list><tree><noCountry><name sortKey="Vorlova, Sandra" sort="Vorlova, Sandra" uniqKey="Vorlova S" first="Sandra" last="Vorlová">Sandra Vorlová</name></noCountry><country name="Allemagne"><noRegion><name sortKey="Bornscheuer, Uwe" sort="Bornscheuer, Uwe" uniqKey="Bornscheuer U" first="Uwe" last="Bornscheuer">Uwe Bornscheuer</name></noRegion><name sortKey="Bertram, Heinz Uergen" sort="Bertram, Heinz Uergen" uniqKey="Bertram H" first="Heinz-Juergen" last="Bertram">Heinz-Juergen Bertram</name><name sortKey="Gatfield, Ian" sort="Gatfield, Ian" uniqKey="Gatfield I" first="Ian" last="Gatfield">Ian Gatfield</name><name sortKey="Hilmer, Jens Ichael" sort="Hilmer, Jens Ichael" uniqKey="Hilmer J" first="Jens-Michael" last="Hilmer">Jens-Michael Hilmer</name><name sortKey="Schmid, Rolf" sort="Schmid, Rolf" uniqKey="Schmid R" first="Rolf" last="Schmid">Rolf Schmid</name><name sortKey="Schmid, Rolf" sort="Schmid, Rolf" uniqKey="Schmid R" first="Rolf" last="Schmid">Rolf Schmid</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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